How an insecure, acid-dropping hippie kid reinvented himself as a technological visionary - and changed the world
When I first met Steve Jobs, I thought he was a loser. It was 1980, and I was just a Silicon Valley kid who knew nothing about computers. I had gotten a job at this little computer company near my house called Apple because my mom worked there. It was based in what looked like an abandoned dentists office on Bandley Drive in Cupertino, just a block or two from Apple's current headquarters. Jobs was 25 at the time, and what I remember about him is how he would storm around the office, yelling, and how he wore tattered jeans, and how everyone seemed to be afraid of him. I knew his type: uneducated, blustery, a guy who thinks a lot of himself. At the time, I had no idea what computers would amount to and no idea that this guy would turn out to be one of the greatest visionaries of our time. To me, he just seemed like a lost hippie kid, and I was not terribly interested. After less than a year at Apple, I left to go on to more exciting things, like dealing blackjack in Lake Tahoe.
It was only a few years before I understood exactly what I had walked away from. Jobs not only turned Apple into the most valued company in the world, worth an estimated $342 billion, he rewrote the rules of business, combining Sixties idealism with greed-is-good capitalism. At a time when software was the model, he built hardware. At a time when everyone focused on the macro, he focused on the micro. He never did anything first, but he did it best. More than anyone else on the planet, he is responsible for fusing the human realm with the digital, for giving us the ability to encode our deepest desires and most intimate thoughts with the touch of a finger. "He's the Bob Dylan of machines," says Bono, who knew Jobs for years. "He's the Elvis of the hardware-software dialectic."
But, God, he could be a dick. Those who knew Jobs best and worked with him most closely - and I have talked to hundreds of them over the years – were always struck by his abrasive personality, his unapologetic brutality. He screamed, he cried, he stomped his feet. He had a cruelly casual way of driving employees to the breaking point and tossing them aside; few people ever wanted to work for him twice. When he fathered a daughter with his longtime girlfriend Chrisann Brennan at age 23, he not only denied his paternity, he famously trashed Brennan in public, telling Time in 1983 that "28 percent of the male population of the United States could be the father." His kinder side would only emerge years later, after he had been kicked around, beaten up, humbled by life. He grew up poor, an adopted kid who felt cast aside by his birth parents, feeling scrawny and teased and out of place, and he remained deeply insecure for most of his life, certain that it would not last long.
"Steve always had that James Dean, live-fast, die-young thing," says Steve Capps, one of the key programmers on the first Apple Macintosh. As they worked late into the night to design and build the device that would revolutionize personal computing, Jobs would talk about death a lot. "It was a little morbid," Capps recalls. "He'd say, 'I don't want to be 50.'" Brennan recalls Jobs making similar comments when he was only 17. "Steve always believed he was going to die young," Brennan says. "I think that's part of what gave his life such urgency. He never expected to live past 45."
In 2005, not long after he was diagnosed with the cancer that would eventually kill him, Jobs gave a now-famous commencement address at Stanford University in which he hailed death as "very likely the single best invention of life," one that "clears out the old to make way for the new." Perhaps it was not unexpected that Jobs, the archetype of the modern inventor, would conceive of death in such terms – as if life itself were an idea that had been hacked together by a larger, more powerful version of himself in some big garage in the sky. But if death is life's greatest invention, the greatest invention of Steve Jobs was not the iPod or the iPhone or the iPad. It was Steve Jobs. Before he could alter the landscape of the world as he found it, he first had to design and assemble the Jobs the world would come to idolize. "Steve was a shallow, narcissistic person who became more fully developed emotionally as he went along," says John Perry Barlow, a digital pioneer and former lyricist for the Grateful Dead who knew Jobs for several decades. "He created a lot of great hardware, but over the years, he also invented himself."
Jobs was born to insecurity. His mother, Joanne Schieble, was a graduate student at the University of Wisconsin, where she got involved with a Syrian student named Ab-dulfattah Jandali. When Schieble found out she was pregnant, her father objected to her marrying a Syrian. "Without telling me, Joanne upped and left to move to San Francisco to have the baby without anyone knowing, including me," Jandali would later tell a reporter. "She did not want to bring shame onto the family and thought this was the best for everyone."
Steven Paul Jobs was born on February 24th, 1955. Schieble gave her baby up to Paul and Clara Jobs, a working-class couple in San Francisco. Paul, a high school dropout who grew up on a farm in Wisconsin, made his living as a debt collector, a repo man and a machinist. Clara worked as a payroll clerk at Varian Associates, one of the first high-tech companies in Silicon Valley. It was not what Schieble wanted for her child, but she made one provision for him before she left. The first in her family to go to college, Schieble believed in the value of education: Before she signed the adoption papers, she made Paul and Clara promise to send her son to college.
From the start, Jobs was a temperamental kid. He jammed bobby pins into an electric outlet and burned his hand. He had to have his stomach pumped after he drank ant poison. He woke up early, so his parents got him a rocking horse, a gramophone and some Little Richard records to entertain himself. "He was so difficult a child," his mother would later confide to Brennan, "that by the time he was two, I felt we had made a mistake, and I wanted to return him." Like many other parents of the time, Paul and Clara soon plunked their son down in front of a relatively new technology called television, where he eagerly devoured everything from Dobie Gillis and I Love Lucy to Jonny Quest.
When Jobs was three, Paul moved the family from San Francisco to Mountain View, an unsophisticated town of tract houses and apricot orchards just south of Palo Alto. It turned out to be a fortuitous move, putting young Steve right in the middle of the engineering culture that was just beginning to blossom in Silicon Valley. Not that the Jobs family had much connection to it. Paul tried fixing up old cars and dabbling in real estate, but money always seemed to elude him. In the fourth grade, Steve's teacher, Imogene Hill, asked the class, "What is it in this universe that you don't understand?" When it came to Steve's turn to answer, his reply was heartbreaking: "I don't understand why all of a sudden we're so broke."
Jobs was too mouthy and inattentive to be a great student. But he was saved from truancy and delinquency by Hill. "She was one of the saints of my life," he would later recall. "She taught an advanced fourth-grade class, and it took her about a month to get hip to my situation. She bribed me into learning." Hill paid Steve $5 bills out of her own pocket to do his homework and read. Spurred by her confidence in him, he skipped the fifth grade and went straight into Crittenden Middle School. It proved a rough place for a thin, wispy kid who was never much of an athlete. The other children taunted Jobs about his adoption. "What happened?" they would sneer. "Didn't your mother love you?" When he would recount the teasing years later, his girlfriend Chrisann recalls, "the pain of it still showed on his face."
At 11, Jobs announced to his parents that he was not going back to Crittenden. But instead of telling him to tough it out, Paul and Clara moved the family to Los Altos, a richer town a few miles away, with a better school system. It was in those years that what we now know as Silicon Valley came into being. The orchards that had covered the Valley had recently been bulldozed, and there was a sense of a new world rising, a belief that you could engineer your own future. There were no stuffy traditions, no cultural baggage. You could be whatever or whoever you wanted to be.
Jobs recalled it as a place where everyone was tinkering away in their garages, building their own TVs and stereos with mail-order kits called Heathkits. "These Heathkits would come with these detailed manuals about how to put this thing together, and all the parts would be laid out in a certain way and color-coded," he said. "You'd actually build this thing yourself. It gave one an understanding of what was inside a finished product and how it worked. But maybe even more importantly, it gave one the sense that one could build the things that one saw around oneself in the universe. You looked at a tele-vision set and you would think, 'I haven't built one of those, but I could.' It gave a tremendous level of self-confidence."
When Jobs was 14, a neighbor introduced him to an older kid named Steve Wozniak who was building a little computer board he called the Cream Soda Computer. "Typically, it was really hard for me to explain to people the kind of design stuff I worked on," Wozniak later recalled. "But Steve got it right away. And I liked him. He was kind of skinny and wiry and full of energy."
Wozniak, five years older than Jobs, was a full-on geek: big, socially awkward, obsessed with electronics, a kind of genius at seeing how wires connected and how to make machines dance. Jobs was never as technically sophisticated, but he knew enough to be fascinated. He and Woz hung out in the way boys do, goofing off and playing pranks; they once hung a huge middle finger they had fashioned out of tie-dyed bedsheets on the school building. But they soon graduated to a pastime that barely had a name in those days: phone phreaking, one of the earliest forms of hacking. After reading an article in Esquire, Wozniak and Jobs figured out how to build small blue boxes that mimicked the tones used by phone operators – enabling users to place free long distance calls at will. According to legend, Wozniak used a blue box to phone the Vatican; adopting a German accent, he identified himself as Henry Kissinger and asked to speak to the pope.
Other geeky kids might have left it at that – a fun toy for impressing your friends with stupid pranks. But even then, Jobs saw the commercial potential in cool technology. He and Woz sold the boxes in the dorms on the Berkeley campus of the University of California, making some nice pocket money before giving it up for fear of getting busted. It was an early test run at entrepreneurship. Jobs later said that without the blue boxes, there would be no Apple.
In 1972, when he was 17, Jobs met a green-eyed bohemian girl named Chrisann Brennan who was a year behind him at Homestead High. They soon embarked on a big, messy teenage romance, taking LSD at school and talking about The Pri-mal Scream, a book by Arthur Janov. For Jobs, dropping acid was not only a means to living life more fully – it was a way to overcome the pain of being abandoned by his birth parents. "Steve explained to me how both LSD and primal screaming opened up stored trauma in the medulla," Chrisann writes in an unpublished memoir she shared with Rolling Stone. "He would repeatedly talk about Janov's ideas in regard to how mothers and fathers would fail to love their children and walk out on them in so many ways, creating and perpetuating trauma." Jobs was quiet and funny, so shy that Chrisann had to initiate kissing. He would play guitar for her in his bedroom, crooning like his hero, Bob Dylan. From the beginning, it was clear to Brennan that Jobs was going places. "He told me on our first or second date that he would be a millionaire someday, and I believed him," says Brennan. "Steve could see the future."
Unlike Wozniak, who was content to remain within the boundaries of his geeky life, Jobs was a searcher. He watched art movies and wrote poetry. He chased girls and had lots of sex. He experimented with sleep deprivation, fasting and drugs. "What is this I found in your car?" Paul Jobs asked his son at one point. Steve didn't even try to hide the truth. "That's marijuana, Father," he said. The summer after high school, Steve and Chrisann left home and moved into a cabin in the mountains above Cupertino, where Jobs typed late into the night, rewriting Dylan lyrics in his own words.
Jobs knew that his parents had promised his birth mother they would send him to college, and he took the obligation seriously. In 1972, he left Chrisann to enroll in Reed College, a private school in Oregon known for its free spirits and hippie vibe. But by the end of the first semester, he'd dropped out. "After six months, I couldn't see the value in it," he recalled. "I had no idea what I wanted to do with my life and no idea how college was going to help me figure it out. And here I was spending all of the money my parents had saved their entire life. So I decided to drop out and trust that it would all work out OK."
Jobs hung around Reed for another six months or so, auditing a class in calligraphy. It was hardly the kind of thing a budding entrepreneur would be expected to study, but Jobs was after enlightenment, not career advancement. "I didn't have a dorm room, so I slept on the floor in friends' rooms," he later recalled. "I returned Coke bottles for the five-cent deposits to buy food with, and I would walk the seven miles across town every Sunday night to get one good meal a week at the Hare Krishna temple. I loved it."
Jobs came to see himself as part of the tail end of the Sixties idealism. "We wanted to more richly experience why we were alive, not just make a better life," he said of his generation. "So people went in search of things. The great thing that came from that time was to realize that there was definitely more to life than the materialism of the late Fifties and early Sixties. We were going in search of something deeper."
At the time, it seemed that all young searchers ended up in the same place: India. At Reed, Jobs was introduced to the teachings of Neem Karoli Baba, an Indian guru whose ideas had been popularized by author Ram Dass in a best-seller called Be Here Now. Before long, Jobs had embarked on a pilgrimage to India to meet Baba, but the guru died shortly before he arrived. Jobs shaved his head, trekked through the Himalayas and spent a month living in a one-room cement hut on a potato farm. During his wanderings, overcome by the widespread poverty and suffering he encountered, he was struck by an insight that would prove central to his own reinvention, a subtle but significant shift from the spiritual to the practical: "It was one of the first times I started thinking that maybe Thomas Edison did a lot more to improve the world than Karl Marx and Neem Karoli Baba put together."
The story of the birth of Apple is so well-known that it can practically be recited by schoolchildren: the Homebrew Computer Club, Jobs and Wozniak building the first computer in his parents' garage, naming the company after an apple farm in Oregon that Jobs visited briefly when he returned from India. It's the stuff of Silicon Valley legend.
At Apple, the division of labor was clear: Wozniak was the technical brains, Jobs was the hustler. Jobs pushed Woz to finish his projects and scored the necessary parts at rock-bottom prices; he would later say he learned to negotiate by watching his dad haggle for auto parts at junkyards. From the start, it was Jobs who had the imagination to see that there was a business to be built on personal computers. In some ways, it was a measure of desperation: He was broke, and he needed money. In other ways, it was the extension of the Heathkit impulse that reigned in the Valley in those days: You could build anything, including your very own company.
For Jobs, the model of a successful startup was Atari, the video-game company where he had worked when he was saving money for his trip to India. But Jobs fused Atari's get-rich-quick entre-preneurialism with a Sixties seeking of enlightenment. Larry Brilliant, who met Jobs in India and later went on to run a variety of philanthropic ventures in the Valley, recalls asking Jobs why an idealistic guy like him was starting up a for-profit company. "Remember in the Sixties, when people were raising their fists and saying, 'Power to the people'?" Jobs told him. "Well, that's what I'm doing with Apple. By building affordable personal computers and putting one on every desk, in every hand, I'm giving people power. They don't have to go through the high priests of mainframe - they can access information themselves. They can steal fire from the mountain. And this is going to inspire far more change than any nonprofit."
It's an open question how much Jobs believed his own high-blown rhetoric, and how much of it was simply clever marketing spin. Either way, his fusion of idealism and technology was right for the times: Apple took off. Jobs was worth $10 million by the time he was 24; a year later, he was worth more than $100 million.
But as Apple ascended, Jobs changed. Friends say his temper grew shorter, and he began treating those around him badly. He had resumed his relationship with Brennan, and the two of them were living together in a house Jobs had rented not far from Apple. Then, just as Apple was taking off in 1977, Brennan became pregnant – and Jobs responded by pushing her out of his life. "He would not talk to me," she recalls. "He would only talk to his lawyer." Jobs refused to provide her with any financial help, yet he was violently opposed to her giving the baby up for adoption and had his friends pressure her not to have an abortion. After his daughter, Lisa, was born, Jobs was a distant father, dropping in on her infrequently. Brennan ended up renting an apartment for $225 a month and living on welfare. Jobs continued to deny paternity until it was confirmed by a DNA test.
At Apple, Jobs displayed a rebelliousness that bordered on self-destructiveness. By the early 1980s, the company had grown large enough that Jobs could no longer control every aspect of it, and the popular Apple II had already run its course. After seeing a prototype of a mouse and desktop icons during a visit to Xerox PARC, a research center in nearby Palo Alto, Jobs came away convinced that all computers would one day operate on such a model. But he couldn't get the top management at Apple to agree, so he simply hijacked a team working on another project, took the best ideas from Xerox and elsewhere, and added some of his own. The result was a renegade team at Apple, hidden away in a building off the main campus, that was tasked with creating the first Macintosh.
The dictum that Jobs issued to the Macintosh team was simple: Build the coolest machine you can. Every day, it seemed, brought a new crisis: The disk drive didn't work, the software was fucked up. Through it all, Jobs drove the team of eight programmers hard, working them day and night for months on end. "You'd work on something all night, and he'd look at it in the morning and say, "That sucks,'" recalls Capps, the Mac programmer. "He'd want you to defend it. If you could, you were doing your job and Steve respected you. If not, he'd blow you out of the water." Driven by his own demons, Jobs became legendary for his ability to humiliate others. "Steve simultaneously has the best and worst qualities of a human being," says Andy Hertzfeld, another key programmer on the Mac team. "They're both in him, simultaneously, living side by side with each other."
A control freak, Jobs demanded perfection and originality in every detail: When he could not find the precise color he wanted for the Mac, he ordered a special beige tint created. "His reverence for shape and sound and contour and creativity did not come from the boardroom," says Bono. "It came from that anarchic, West Coast, fuck-off attitude that rules the 21st century. He wasn't going to make ugly things that made profits. The big lesson for capitalism is that Steve, deep down, did not believe the consumer was right. Deep down, he believed that he was right. And that the consumer would respect a strong aesthetic point of view, even if it wasn't what they were asking for."
The launch of the new computer, with the iconic 1984 commercial that brilliantly positioned the Mac as a tool of liberation, gave the world its first glimpse of Jobs the showman. The machine itself became a huge success, selling more than a million units and transforming the computer industry, but Jobs was increasingly unable to control the company he had created. His instincts were still those of an adolescent – but as he quickly discovered, you can't run a Fortune 500 company like a garage band. Jobs recruited John Sculley, the CEO of Pepsi, to lend a steady hand, but he proved incapable of sharing power with the more experienced executive. The two men clashed constantly. Forced to choose between the rebel hothead and the even-handed adult, the Apple board tossed Jobs overboard. "At 30, I was out," he later recalled. "And very publicly out. What had been the focus of my entire adult life was gone, and it was devastating."
Jobs was deeply wounded by his ouster from Apple. The central trauma of his life, after all, was being given up for adoption by his parents, and now he was being kicked out of his second family, the company he founded. A close friend of Jobs once speculated to me that Steve's drive came from a deep desire to prove that his parents were wrong to give him up. A desire, in short, to be loved - or, more precisely, a desire to prove that he was somebody worth loving. Whatever the psychological impact, it was clear that Jobs was devastated, and he didn't know what to do with himself. He was young, handsome, famous, rich – and lost. He took some time off to travel around Italy and talk about personal computers in the Soviet Union. He had also reached out to his biological mother and discovered that he had a sister – the writer Mona Simpson. The revelation that he had a talented, arty sibling pleased him to no end, and the two of them became fast friends. To his credit, he also used this time to connect with Lisa, his daughter with Chrisann Brennan.
Within a year or so, Jobs had a comeback plan. He decided he was going to build what he called "the perfect company," and it was going to be perfect in every detail, from the stylish logo designed by Yale art professor Paul Rand to the state-of-the-art factory that would churn out desktop supercomputers with unheard-of speed and grace, a wonder of modern manufacturing. Even the name of the company reeked of a kind of hubris: NeXT. Its success would be his revenge on the bozos at Apple who had tossed him out. He would show them.
It was around that time that my path once again crossed with Jobs. As it turned out, my wife had met Mona Simpson while working at a literary magazine, and she told us, very quietly, about how she had learned that Jobs was her brother. She talked about the troubles that Jobs was having remodeling his apartment in the San Remo, and how he encouraged Mona to buy more expensive clothes. She was proud of him, and protective, but in private she referred to him as "the Sun King," because he was so imperious.
In 1986, when Simpson's novel Anywhere But Here was published, the writer and editor George Plimpton threw her a party at his Upper East Side apartment. The party was full of New York literati, as well as Steve and Mona's mother, Joanne. I did not know that Jobs would be there - in fact, when he quietly walked up and joined a conversation I was having with several other writers, I didn't even recognize him. Gone was the jean-clad nerd I had known in the early days of Apple: In his double-breasted suit, his dark hair perfectly groomed, Jobs seemed more a metrosexual playboy than a computer geek. As the evening wore on, I noticed that women swarmed around him, though he appeared not to notice. Away from Silicon Valley, where he had spent his entire life, he actually seemed a bit unsettled - a man who had no trouble going toe-to-toe with big-time CEOs, but who went tongue-tied when confronted with someone as intimidating as a poet.
At NeXT, Jobs succeeded in producing a strikingly distinctive object – but one that proved way too expensive for the market. Consumers who bought NeXT computers still swoon over them, calling them the most beautiful machines ever built – but in the real world, nobody wanted to pay 10 grand for a beautiful machine. Jobs managed to persuade Ross Perot to invest $20 million in NeXT, but within a few years, it was clear that the company's machines were headed for computer museums as artifacts built by an obsessively perfectionist man who had confused art with commerce.
In the spring of 1994, I went to NeXT to interview Jobs for Rolling Stone. The offices, like everything else about the company, were a showcase of perfection, with a glass staircase designed by the celebrated architect I.M. Pei. It was a sunny day, and salty air from the bay blew through the building - but it was spooky as hell, because the place was deserted. There might have been a few last programmers plugging away in some backroom, but I didn't see them. Jobs met me in the conference room, which practically had cobwebs hanging from the whiteboard. He was 39, stocky and jowly, dressed in jeans. It was the first time I'd seen him with a beard. There was a Citizen Kane quality to it all - the formerly great man in the big empty castle. "Steve is a little like the boy who cried wolf," Robert Cringely, an influential Silicon Valley writer, told me at the time. "He has cried revolution one too many times. People still listen to him, but now they are more skeptical."
Part of the skepticism came from the fact that, at that moment, Silicon Valley was changing fast. A year earlier, a hotshot programmer at the University of Illinois named Marc Andreessen had created the first Web browser, and the dot-com revolution was about to take off. There was a sense that something big was on the horizon – something that Jobs seemed to have no part of. Not that he was oblivious: He talked a little about what was then being called "the information superhighway" and astutely noted that the computer was being transformed from "a tool of computation to a tool of communication." But nothing he was doing at NeXT was really connected to the online revolution.
He was clearly still bitter about what had happened at Apple – and he had even more bitterness toward his old nemesis Bill Gates, who, in a cruel bit of irony, was on his way to becoming the richest man in the world thanks to Windows, the operating system that Microsoft had modeled on the Macintosh. Jobs called Microsoft "completely lost" and cast its market dominance - and its stifling effect on innovation – as a threat to the U.S. economy. "Unfortunately, people are not rebelling against Microsoft," he told me. When I asked how he felt about Gates achieving dominance in the industry by essentially ripping off the approach that Jobs had pioneered, he snapped, "The goal is not to be the richest man in the cemetery. It's not my goal, anyway." Later, when I asked him what his goal in life was, he said, "In the broadest context, the goal is to seek enlightenment – however you define it."
As I listened to him, I once again thought of Orson Welles – a great genius who did his best work at 25 and ended up doing TV game shows and commercials for crappy wine. When I asked Jobs how he felt about the comparison, he had the wit to make light of it. "I'm very flattered by that, actually," he said. "I wonder what game show I'm going to be on."
But here's the thing about Jobs: You could never predict when he was going to say something lovely and profound. Near the end of the interview, I asked him how it felt to walk around in the world and see Mac computers everywhere. "The Macintosh was sort of like this wonderful romance in your life you once had - and that produced about 10 million children," he said wistfully. "In a way it will never be over in your life. You'll still smell the romance every morning when you get up. You'll see your children around, and you feel good about it. And nothing will ever make you feel bad about it."
Two things helped Jobs turn his life around. One was meeting Laurene Powell, a tall, blond Jersey girl studying for an MBA who heard him speak at Stanford after he was booted out of Apple. They were married in 1991 in a small Buddhist ceremony at Yosemite National Park and eventually had three kids together. Friends noticed immediately how becoming a family man matured Jobs. "I saw him coming out of a restaurant in Palo Alto, and he had a baby in his arm," says John Perry Barlow. "He was a changed man. He had a sweetness to him, a contemplative quality."
The other was a little company called Pixar. In 1986, the film production company founded by George Lucas was looking to unload high-tech imaging technology that would allow users to render their own 3D graphics. Jobs, enthralled by the technology, picked the division up for a mere $5 million. Taking over as CEO, he turned the graphics division into an animation studio, cut a deal with Disney for distribution, and gave a budding animation genius named John Lasseter and his team the kind of money and creative license he had never granted his employees at Apple. The result, after years of losses, was Toy Story. In 1995, a week after the film's release, Pixar went public and Jobs found himself sitting on stock worth $1.1 billion. Suddenly, Jobs looked like a genius again.
Apple, meanwhile, was struggling to survive. The board had installed a succession of clueless CEOs, who had done a brilliant job of driving the once-great company into irrelevance. I spent a lot of time at Apple in 1996, reporting a story on the decline and fall of the company for Rolling Stone, and Jobs spent hours on the phone with me, giving me his read on what went wrong and why. It was clear that he was personally offended that a guy as square and conventionally minded as CEO Gil Amelio - a veteran of the semiconductor industry, which is nothing at all like the PC industry - was running Apple. For Jobs, it was like a father seeinghis beloved son in the hands of a child molester.
So Jobs staged a comeback. Like many of his greatest accomplishments, it was swift and brutal. He charmed Amelio and the board sufficiently to convince them to buy NeXT's software for $400 million and use it as the basis for Apple's future operating system, which turned out to be OS X. Then he got himself named as an "informal adviser" to the company. Before long, Amelio was vanquished and Jobs was back in charge. He brought in a new board, sympathetic to his ideas for a turnaround.
For Jobs, this was a huge gamble. Apple was so far gone by that point that reviving it was by no means a sure thing. His strategy was simple. First, he halted Apple's disastrous decision to allow other computers to clone Macintosh's operating system. Next, he went humbly to Bill Gates and struck a deal to keep Microsoft software running on the Mac. Finally, he unleashed a talented designer named Jonathan Ive, giving him free rein to build great computers. His first all-new computer, the iMac, was a simple, distinctive, easy-to-use machine that had the playful spirit of the old Macintosh. It was an immediate hit.
Jobs saw clearly that Apple's future was in more than just PCs – it was in building cool hardware and software to deliver all kinds of content, including music and movies. The iPod, which launched in 2001, was the first move in that direction. I went to see Jobs in November 2003, around the time he introduced the Windows version of iTunes, a move that would make him the most influential man in the record industry. I bumped into him in the lobby – he was wearing shorts and Birkenstocks, looking very relaxed - and we took the elevator up to his office on the fourth floor. It was the least glamorous office you could imagine: no wood paneling, no awesome view, no decanter of whiskey, no silly toys or lava lamps. Settling into the conference room, he began to talk, mostly about the move into music.
iTunes, as Jobs saw it, was a way to stop outfits like Napster from enabling users to steal music – by creating the world's largest music store, with every song available instantly at the user's fingertips. Jobs had just browbeaten the record labels into coming on board, but it was still not clear whether iTunes would be selling individual songs or offering unlimited access to subscribers. "I think you could make available the Second Coming in a subscription model," Jobs mused, "and it might not be successful."
But the business aspects of Apple weren't nearly as interesting as his personal reflections. I asked him about Bob Dylan, what his music meant to him. "He was a very clear thinker, and a poet," Jobs said. "He wrote about what he saw and thought. The early stuff is very precise. As he matured, you had to unravel it a bit. But once you did, it was clear as a bell." He talked about bootlegging Dylan in the early days with Woz. I sensed that he was opening up some, so I pushed him by asking if he ever had any doubts about technology, if he believed we were pushing it all too far: genetic research, cloning, all that.
He looked at me and rolled his eyes. "You know – I'd rather just talk about music. These big-picture questions are just – zzzzzzzz," he said, snoring loudly. "I think we're all happier when we have a little music in our lives."
He waved at my tape recorder. "Turn that off," he ordered. "Can we just talk?"
"Sure," I said, turning off the machine.
"I'm just really uncomfortable talking about this. It's not my thing."
"You don't like to think about the past, do you?" I asked.
"I don't have anything against the past," he said. "I just want to focus on the future."
From there, we went into a freewheeling conversation about the news of the day – starting with Arnold Schwarzenegger's election as governor. ("I wish he had a little more business experience," Jobs said.) I asked him if he ever considered running for public office. He broke into a broad smile, and mimicked the voice of a reporter: "Yes, Mr. Jobs, and could you please tell us how many times you've dropped acid?" As we talked, I got the sense of another Steve Jobs, someone less certain, less self-confident. I asked him if he had gone to see Dylan a lot when he was younger. "Never," he said with obvious regret. "I was too busy with Apple." I suddenly understood how narrow his life had been, how much his success had cost him - so focused on one thing, so desperate to make it work.
Somehow, we got onto the topic of Bill Gates, and I asked him if he believed Gates was greedy. "I like Bill, but sometimes I wonder – Bill, why do you have to take a dollar out of every dollar that passes through your hands? Why do you have to have it all? Can't you just take, like, 99 cents and leave a penny for someone else?"
He seemed unusually relaxed, in no hurry to end the interview. I thought of a question I had always wanted to ask him.
"Where does your common-man touch for technology come from?"
'Yeah, you know – simplicity of design. You understand how people use technology in a human way. Where does that come from?"
"You make it sound like I have statues of Chairman Mao on my front lawn," he said, laughing.
"No, I'm serious."
"I don't think it's that profound. I think most people in the technology world don't pay attention to design. They don't know anything about design, they don't care about it."
Suddenly I could see he was getting impatient, that my time was running out.
"Do you have any regrets about your life?"
"Sure," he said.
"Personal things. Things that have to do with family." I presumed he was talking about Lisa, but I didn't push it.
At this point, my notes falter. I don't remember exactly how we got to this, what it was I asked him that prompted the response. Maybe I asked him if there were things he'd do differently. Maybe I asked him if he felt lucky. Maybe I even asked him if he was afraid of dying. But what I remember is this: Jobs leaning forward at the end of the table and looking at me directly, his eyes intense. "I think that life is something that happens in a flash," he said. He snapped his fingers. "We just have a brief moment here, and then we are gone."
As I said goodbye, he gave me a long look in the eye. I'm not sure what it meant, but there was a humanness to him that I had not seen before. I could see that he was confused and vulnerable. He had made sacrifices, done things wrong, had regrets. What he had shared with me were not the breathtaking thoughts of a visionary, but those of a regular human being.
Only a month earlier, he had been diagnosed with pancreatic cancer.
Jobs never expected to live past his forties. He had more than a passing interest in Buddhism, which teaches that death is not necessarily final - that souls can be reincarnated. Still, for a father with four children, the diagnosis was a brutal blow.
Most people who get pancreatic cancer are dead within a few months. But Jobs got lucky, as he often did. His cancer, a rare neuroendocrine tumor, was slower-growing than most, giving him more time to seek treatment. Instead of fearing death, Jobs embraced it as a tool to clarify his thinking. "Remembering that I'll be dead soon is the most important tool I've ever encountered to help me make the big choices in life," he said in his commencement address at Stanford University. "Because almost everything – all external expectations, all pride, all fear of embarrassment or failure – these things just fall away in the face of death, leaving only what is truly important."
As always, Jobs sought his ultimate solace in his work. Two of Apple's most innovative and successful products - the iPhone and the iPad – were both launched after he was diagnosed with cancer. Both were risky ventures that could easily have flopped, but Jobs retained his perfectionist discipline. Vic Gondotra, head of mobile applications at Google, was attending religious services one Sunday morning when he got a call from Jobs. "I've been looking at the Google logo on the iPhone, and I'm not happy with the icon," Jobs told him. "The second 'o' in Google doesn't have the right yellow gradient. It's just wrong and I'm going to have Greg fix it tomorrow. Is that OK with you?" Gondotra calls it a lesson he'll neverforget. "CEOs should care about details," he says. "Even shades of yellow. On a Sunday."
As his illness worsened, Jobs found his life narrowing even further. He didn't go out at night, never accepted awards, gave no speeches, attended no parties. Instead, he holed up in his home in Palo Alto, where he hung out with his family and learned everything he could about cancer – and how he might beat it. "He knew more about it than any oncologist," says his old friend Larry Brilliant, who is an M.D. His body grew thinner and thinner, and he took a six-month leave from Apple to have a liver transplant.
Late last year, Jobs called me out of the blue to ask about doing another magazine story together. I was struck by how different his voice sounded on the phone. It was not just softer and weaker. It was also more curious. For the first time, he asked me about my kids. I have no idea how he even knew that I have kids – we'd never discussed it. Others noticed the same change in his manner. He no longer seemed as arrogant, and had lots of time and compassion for the suffering of others. When Brilliant's 24-year-old son developed what turned out to be a fatal cancer, Jobs became his "cancer buddy," Brilliant says. Jobs made spreadsheets detailing the pros and cons of various doctors to help him decide whom to see. He called every week, talking Brilliant's son through the chemo, saying, "If I can make it through this, so can you." "Whenever he was down, Steve would call and give him a pep talk to buoy his spirits," recalls Brilliant.
At the iPad launch in January 2010, Jobs was accompanied by his family, including his wife, Laurene, and his sister, Mona. Onstage, he worked through his presentation, looking thin and frail, but courageous. His body was rail-thin, his cheeks gaunt. After the talk, Jobs pulled on a black hoodie and went into the demo area to talk to the media. When I stopped to say hello, he looked at me with glazed eyes – the faraway, unfocused eyes of an old man – and said, "What do you think of the iPad?" I wasn't sure if he recognized me, and it was clear he was having a hard time carrying on a conversation. Apple's PR people quickly whisked him away, and I never spoke to him again.
For Jobs, the slide continued. Brilliant stopped by his house frequently. On good days, they would walk downtown to get a smoothie, the only food Jobs could eat. "We laughed a lot," Brilliant says. "Sometimes we would talk about God, or about the afterlife – which Steve was intensely curious about. He was very frank about what was going on. He was not in any kind of denial." Jobs often had IVs strapped to his arms. "I'd joke with him that from the neck up, he looked great," says Brilliant. "But his legs looked like Bam-bi's." Sometimes, when the talk got heavy, Brilliant – who is not a small man – would crawl onto the bed beside Jobs and hold him. "He was not worried about Apple's future – he knew that would be fine," Brilliant says. "He was thinking about his kids. He said to me, 'I just want to live long enough to see my kids graduate from high school.'"
According to Brilliant, Jobs had come very close to death twice over the summer: "He had gathered his family around him to say goodbye." Somehow, he rallied both times, but the trajectory was clear. Only a few people were allowed to see him in his final days – beyond his immediate family, the list included Dr. Dean Ornish, a close friend, and John Doerr, the venture capitalist. Brilliant last saw him two weeks before he died. In his room, Jobs had two pictures of the guru he never got to meet, Neem Karoli Baba, as well as a book of Baba's teachings, Miracle of Love. Although he was frightfully thin, Brilliant says, Jobs was "mutedly optimistic" that he would make it, that the new cancer treatment he was taking might buy him more time. "When I left," Brilliant says, "it did not feel like goodbye."
Jobs died at home on Wednesday, October 5th, surrounded by his family. He was 56 years old. He had always known he would never live to be an old man, but he came closer than he ever imagined he would. He used the extra years - "borrowed time," he called it – to complete the spiritual journey he had begun as a kid in the apricot orchards of Silicon Valley. "There were those two sides to him," says Bono, who spoke to Jobs not long before he died. "There was the warrior, and then there was the very tender and soft-spoken side. I already miss him." Jobs may be remembered as the man who brought the human touch to our digital devices. But perhaps his greatest – and hardest-won – accomplishment was bringing the human touch to Steve Jobs.
This story is from the October 27th, 2011 issue of Rolling Stone.